ES2548764T3 - Benzimidazole cannabinoid agonists - Google Patents

Benzimidazole cannabinoid agonists Download PDF

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ES2548764T3
ES2548764T3 ES08718169.9T ES08718169T ES2548764T3 ES 2548764 T3 ES2548764 T3 ES 2548764T3 ES 08718169 T ES08718169 T ES 08718169T ES 2548764 T3 ES2548764 T3 ES 2548764T3
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4alkyl
4alkyloxy
polyhalo
amino
hydroxy
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Henricus Jacobus Maria Gijsen
Michel Anna Jozef De Cleyn
Michel Surkyn
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Janssen Pharmaceutica NV
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    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
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    • C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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    • C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings

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  • Health & Medical Sciences (AREA)
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  • Diabetes (AREA)
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  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

Compuesto de fórmula (I) incluida cualquier forma estereoquímicamente isomérica del mismo, en donde n es un número entero 0, 1 ó 2; X es SO, SO2 o N-(CO)-R1; R1 es hidrógeno; alquilo C1-6; alquiloxi C1-6; alquiloxi C1-4-alquiloC1-4; o polihalo-alquilo C1-6; R2 es alquilo C1-6; R3 es hidrógeno, halo, alquilo C1-4, alquiloxi C1-4, trifluorometilo o ciano; R4 es alquilo C1-8; alquilo C1-8 sustituido con cicloalquilo C3-8; polihalo-alquilo C1-8; alquilo C1-8 sustituido con 1, 2 ó 3 sustituyentes seleccionados, cada uno independientemente, de hidroxi, alquiloxi C1-4, polihalo-alquiloxi C1-4, ciano, nitro, tetrahidropiranilo, tetrahidrofuranilo, oxetanilo, arilo o heteroarilo; cicloalquilo C3-8; cicloalquilo C3-8 sustituido con 1, 2 ó 3 sustituyentes seleccionados, cada uno independientemente, de hidroxi, alquiloxi C1-4, polihalo-alquiloxi C1-4, ciano, nitro, tetrahidropiranilo, tetrahidrofuranilo, oxetanilo, arilo o heteroarilo; tetrahidropiranilo, tetrahidrofuranilo, oxetanilo, arilo; o heteroarilo; arilo es fenilo; o fenilo sustituido con 1, 2 ó 3 sustituyentes seleccionados, cada uno independientemente, de halo, hidroxi, alquilo C1-4, polihalo-alquilo C1-4, alquiloxi C1-4, polihalo-alquiloxi C1-4, ciano, nitro, NR5R6, R7- carbonilo, R7-SO2-, o alquilo C1-4 sustituido con hidroxi, NR5R6, R7-carbonilo o R7-SO2-; heteroarilo se selecciona de furanilo, tiofenilo, pirrolilo, pirazolilo, imidazolilo, isoxazolilo, tiazolilo, triazolilo, tetrazolilo, isotiazolilo, tiadiazolilo, oxadiazolilo, piridinilo, piridazinilo, pirimidinilo o pirazinilo; en donde R5 y R6 se seleccionan, independientemente de otro, de hidrógeno, alquilo C1-4, polihalo-alquilo C1-4, aminosulfonilo o alquil C1-8-sulfonilo; o R7 carbonilo; en donde R5 y R6, tomados junto con el átomo de nitrógeno que porta R5 y R6, pueden formar un anillo pirrolidinilo, piperidinilo, piperazinilo o morfolinilo; y en donde R7 es alquilo C1-4, hidroxi, amino, amino, mono- o di-(alquil C1-4)amino, (hidroxi-alquil C1-4)amino, (alquiloxi C1-4,-alquil C1-4)amino, di-(alquil C1-4)amino-alquilo C1-4, pirrolidinilo, piperidinilo, morfolinilo, o N-metil-piperazinilo; o una sal por adición de ácidos farmacéuticamente aceptable del mismo, o un solvato del mismo.Compound of formula (I) including any stereochemically isomeric form thereof, wherein n is an integer 0, 1 or 2; X is SO, SO2 or N- (CO) -R1; R1 is hydrogen; C1-6alkyl; C1-6 alkyloxy; C1-4alkyloxy-C1-4alkyl; or polyhalo-C1-6alkyl; R2 is C1-6 alkyl; R3 is hydrogen, halo, C1-4alkyl, C1-4alkyloxy, trifluoromethyl or cyano; R4 is C1-8 alkyl; C1-8alkyl substituted with C3-8cycloalkyl; polyhalo-C1-8-alkyl; C1-8alkyl substituted with 1, 2 or 3 substituents each independently selected from hydroxy, C1-4alkyloxy, polyhalo-C1-4alkyloxy, cyano, nitro, tetrahydropyranyl, tetrahydrofuranyl, oxetanyl, aryl or heteroaryl; C3-8 cycloalkyl; C3-8cycloalkyl substituted with 1, 2 or 3 substituents, each independently selected from hydroxy, C1-4alkyloxy, polyhalo-C1-4alkyloxy, cyano, nitro, tetrahydropyranyl, tetrahydrofuranyl, oxetanyl, aryl or heteroaryl; tetrahydropyranyl, tetrahydrofuranyl, oxetanyl, aryl; or heteroaryl; aryl is phenyl; or phenyl substituted with 1, 2, or 3 selected substituents, each independently, of halo, hydroxy, C1-4alkyl, polyhalo-C1-4alkyl, C1-4alkyloxy, polyhalo-C1-4alkyloxy, cyano, nitro, NR5R6 , R7-carbonyl, R7-SO2-, or hydroxy substituted C1-4alkyl, NR5R6, R7-carbonyl or R7-SO2-; Heteroaryl is selected from furanyl, thiophenyl, pyrrolyl, pyrazolyl, imidazolyl, isoxazolyl, thiazolyl, triazolyl, tetrazolyl, isothiazolyl, thiadiazolyl, oxadiazolyl, pyridinyl, pyridazinyl, pyrimidinyl, or pyrazinyl; wherein R5 and R6 are independently selected from hydrogen, C1-4alkyl, polyhalo-C1-4alkyl, aminosulfonyl or C1-8alkyl-sulfonyl; or R7 carbonyl; wherein R5 and R6, taken together with the nitrogen atom bearing R5 and R6, can form a pyrrolidinyl, piperidinyl, piperazinyl, or morpholinyl ring; and wherein R7 is C1-4alkyl, hydroxy, amino, amino, mono- or di- (C1-4alkyl) amino, (hydroxy-C1-4alkyl) amino, (C1-4alkyloxy, -C1-4alkyl ) amino, di- (C1-4alkyl) amino-C1-4alkyl, pyrrolidinyl, piperidinyl, morpholinyl, or N-methyl-piperazinyl; or a pharmaceutically acceptable acid addition salt thereof, or a solvate thereof.

ES08718169.9T 2007-03-30 2008-03-25 Benzimidazole cannabinoid agonists Active ES2548764T3 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
EP07105286 2007-03-30
EP07105286 2007-03-30
PCT/EP2008/053480 WO2008119694A1 (en) 2007-03-30 2008-03-25 Benzimidazole cannabinoid agonists

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ES2548764T3 true ES2548764T3 (en) 2015-10-20

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US (1) US8193369B2 (en)
EP (1) EP2142531B1 (en)
JP (1) JP5504153B2 (en)
CN (1) CN101679355B (en)
AR (1) AR065872A1 (en)
CL (1) CL2008000906A1 (en)
ES (1) ES2548764T3 (en)
PA (1) PA8773601A1 (en)
TW (1) TW200901980A (en)
WO (1) WO2008119694A1 (en)

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CN102292328A (en) 2009-01-22 2011-12-21 拉夸里亚创药株式会社 N-substituted saturated heterocyclic sulfone compounds with cb2 receptor agonistic activity
CA2770866C (en) 2009-08-28 2017-10-10 Arena Pharmaceuticals, Inc. Cannabinoid receptor modulators
AU2012222149B2 (en) 2011-02-25 2017-06-29 Arena Pharmaceuticals, Inc. Cannabinoid receptor modulators
WO2012116277A1 (en) 2011-02-25 2012-08-30 Arena Pharmaceuticals, Inc. Cannabinoid receptor modulators
EA035989B1 (en) 2011-02-25 2020-09-09 Арена Фармасьютикалз, Инк. Crystalline forms and processes for the preparation of cannabinoid receptor modulators
WO2015081188A1 (en) * 2013-11-27 2015-06-04 Olatec Industries Llc Pharmaceutical composition comprising omega-(arylsulfonyl)alkylnitrile
WO2022128050A1 (en) 2020-12-14 2022-06-23 Symrise Ag Medicament for fighting inflammation and pain

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SE0302572D0 (en) 2003-09-26 2003-09-26 Astrazeneca Ab Benzimidazole derivatives, compositions containing them, preparation thereof and uses thereof
ATE417830T1 (en) 2004-11-02 2009-01-15 Pfizer SULFONYLBENZIMIDAZOLE DERIVATIVES
TW200745096A (en) * 2005-08-23 2007-12-16 Organon Nv Indole derivatives
JP5345528B2 (en) * 2006-07-04 2013-11-20 ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ Benzimidazole cannabinoid agonists with substituted heterocyclic groups

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CL2008000906A1 (en) 2008-10-03
TW200901980A (en) 2009-01-16
US20100041702A1 (en) 2010-02-18
CN101679355A (en) 2010-03-24
PA8773601A1 (en) 2008-11-19
EP2142531A1 (en) 2010-01-13
CN101679355B (en) 2014-01-29
JP2010523482A (en) 2010-07-15
US8193369B2 (en) 2012-06-05
JP5504153B2 (en) 2014-05-28
AR065872A1 (en) 2009-07-08
WO2008119694A1 (en) 2008-10-09

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